Structure

Physi-Chem Properties

Molecular Weight:  684.41
Volume:  682.719
LogP:  2.059
LogD:  2.606
LogS:  -3.162
# Rotatable Bonds:  6
TPSA:  206.6
# H-Bond Aceptor:  12
# H-Bond Donor:  8
# Rings:  6
# Heavy Atoms:  12

MedChem Properties

QED Drug-Likeness Score:  0.188
Synthetic Accessibility Score:  5.703
Fsp3:  0.972
Lipinski Rule-of-5:  Rejected
Pfizer Rule:  Accepted
GSK Rule:  Rejected
BMS Rule:  1
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -5.885
MDCK Permeability:  3.450502481427975e-05
Pgp-inhibitor:  0.934
Pgp-substrate:  0.009
Human Intestinal Absorption (HIA):  0.796
20% Bioavailability (F20%):  0.384
30% Bioavailability (F30%):  0.824

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.108
Plasma Protein Binding (PPB):  77.30818176269531%
Volume Distribution (VD):  0.439
Pgp-substrate:  6.769106388092041%

ADMET: Metabolism

CYP1A2-inhibitor:  0.003
CYP1A2-substrate:  0.676
CYP2C19-inhibitor:  0.001
CYP2C19-substrate:  0.573
CYP2C9-inhibitor:  0.003
CYP2C9-substrate:  0.037
CYP2D6-inhibitor:  0.002
CYP2D6-substrate:  0.098
CYP3A4-inhibitor:  0.053
CYP3A4-substrate:  0.066

ADMET: Excretion

Clearance (CL):  1.098
Half-life (T1/2):  0.733

ADMET: Toxicity

hERG Blockers:  0.116
Human Hepatotoxicity (H-HT):  0.34
Drug-inuced Liver Injury (DILI):  0.017
AMES Toxicity:  0.102
Rat Oral Acute Toxicity:  0.215
Maximum Recommended Daily Dose:  0.022
Skin Sensitization:  0.289
Carcinogencity:  0.044
Eye Corrosion:  0.003
Eye Irritation:  0.02
Respiratory Toxicity:  0.975

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Structure MOL file  
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Biological Activities  
Similar NPs/Drugs  

  Natural Product: NPC203974

Natural Product ID:  NPC203974
Common Name*:   Gentirigeoside A
IUPAC Name:   (2S,4S,5S)-4,5-dihydroxy-2-[(3S,4S,5R,8R,9R,10R,13R,14R,17S)-4-(hydroxymethyl)-4,8,10,14-tetramethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-6,6-dimethyloxane-2-carboxylic acid
Synonyms:  
Standard InCHIKey:  XPJOLTRXAYBSEB-KMWDMBMQSA-N
Standard InCHI:  InChI=1S/C36H60O12/c1-31(2)28(43)20(39)15-36(48-31,30(44)45)19-9-13-34(5)18(19)7-8-23-32(3)12-11-24(33(4,17-38)22(32)10-14-35(23,34)6)47-29-27(42)26(41)25(40)21(16-37)46-29/h18-29,37-43H,7-17H2,1-6H3,(H,44,45)/t18-,19+,20+,21-,22-,23-,24+,25-,26+,27-,28+,29+,32+,33-,34-,35-,36+/m1/s1
SMILES:  CC1(C)[C@H]([C@H](C[C@]([C@H]2CC[C@]3(C)[C@@H]2CC[C@@H]2[C@@]4(C)CC[C@@H]([C@](C)(CO)[C@@H]4CC[C@@]32C)O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)(C(=O)O)O1)O)O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL373538
PubChem CID:   44422964
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000012] Lipids and lipid-like molecules
      • [CHEMONTID:0000259] Prenol lipids
        • [CHEMONTID:0002049] Terpene glycosides
          • [CHEMONTID:0001580] Triterpene glycosides
            • [CHEMONTID:0002358] Triterpene saponins

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO18234 Gentiana rigescens Species Gentianaceae Eukaryota roots n.a. n.a. PMID[17375953]
NPO18234 Gentiana rigescens Species Gentianaceae Eukaryota n.a. n.a. n.a. PMID[20813533]
NPO17493 Alstonia spatulata Species Apocynaceae Eukaryota n.a. leaf n.a. PMID[21043460]
NPO17493 Alstonia spatulata Species Apocynaceae Eukaryota n.a. n.a. n.a. PMID[21043460]
NPO17493 Alstonia spatulata Species Apocynaceae Eukaryota n.a. stem n.a. PMID[21043460]
NPO32460 Gentianella azurea Species Gentianaceae Eukaryota n.a. n.a. n.a. PMID[24806310]
NPO32460 Gentianella azurea Species Gentianaceae Eukaryota n.a. n.a. n.a. PMID[25442320]
NPO27624 Swartzia simplex Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[26654828]
NPO12009 Abies pinsapo Species Pinaceae Eukaryota Wood n.a. n.a. PMID[7931362]
NPO17493 Alstonia spatulata Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18843 Antirrhinum majus Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16073 Sarcomelicope megistophylla Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19120 Strychnos aculeata Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18234 Gentiana rigescens Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15856 Podocarpus hallii Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16646 Artemisia campestris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17368 Erythrina senegalensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO19120 Strychnos aculeata Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16817 Aglaia argentea Species Meliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17368 Erythrina senegalensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15856 Podocarpus hallii Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18234 Gentiana rigescens Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17493 Alstonia spatulata Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16073 Sarcomelicope megistophylla Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16646 Artemisia campestris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18843 Antirrhinum majus Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18843 Antirrhinum majus Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18234 Gentiana rigescens Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16646 Artemisia campestris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15856 Podocarpus hallii Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18234 Gentiana rigescens Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15856 Podocarpus hallii Species Podocarpaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18511 Latimeria chalumnae Species Coelacanthidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17368 Erythrina senegalensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17711 Sphenoclea zeylanica Species Sphenocleaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27624 Swartzia simplex Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16073 Sarcomelicope megistophylla Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14721 Dentitheca habereri Species Plumulariidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16646 Artemisia campestris Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17493 Alstonia spatulata Species Apocynaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3046 Schisandra bicolor Species Schisandraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17699 Solanum glaucophyllum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17054 Streptomyces gardneri Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO16958 Jurinea albicaulis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18234 Gentiana rigescens Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18372 Lobophytum crassospiculatum Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18843 Antirrhinum majus Species Plantaginaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15518 Streptomyces netropsis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO16817 Aglaia argentea Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13251 Iris nertchinskia Species Tarachodidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12009 Abies pinsapo Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19120 Strychnos aculeata Species Loganiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  NP Quantity Composition/Concentration

Organism ID NP ID Organism Material Preparation Organism Part NP Quantity (Standard) NP Quantity (Minimum) NP Quantity (Maximum) Quantity Unit Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT113 Cell Line RAW264.7 Mus musculus IC50 = 6600.0 nM PMID[461246]
NPT20529 NON-MOLECULAR NON-PROTEIN TARGET n.a. IZ = 20.0 mm PMID[461245]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

  Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

●  The left chart: Distribution of similarity level between NPC203974 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
0.98 High Similarity NPC236753
0.98 High Similarity NPC228190
0.9184 High Similarity NPC472273
0.9159 High Similarity NPC179429
0.9126 High Similarity NPC472079
0.9126 High Similarity NPC469826
0.9048 High Similarity NPC469824
0.8962 High Similarity NPC477489
0.8922 High Similarity NPC34562
0.8857 High Similarity NPC208333
0.8857 High Similarity NPC227879
0.8835 High Similarity NPC469827
0.8812 High Similarity NPC20028
0.8788 High Similarity NPC94582
0.8788 High Similarity NPC57964
0.875 High Similarity NPC215408
0.8725 High Similarity NPC477172
0.87 High Similarity NPC237071
0.87 High Similarity NPC238796
0.87 High Similarity NPC203434
0.8692 High Similarity NPC473062
0.8679 High Similarity NPC469825
0.8667 High Similarity NPC126753
0.8661 High Similarity NPC470478
0.8641 High Similarity NPC310031
0.8641 High Similarity NPC80191
0.8624 High Similarity NPC477465
0.8624 High Similarity NPC79193
0.8611 High Similarity NPC477492
0.86 High Similarity NPC215570
0.8598 High Similarity NPC470622
0.8585 High Similarity NPC202898
0.8585 High Similarity NPC92890
0.8585 High Similarity NPC475319
0.8558 High Similarity NPC107385
0.8515 High Similarity NPC296936
0.8505 High Similarity NPC94086
0.8505 High Similarity NPC233433
0.8505 High Similarity NPC220836
0.8505 High Similarity NPC273002
0.8505 High Similarity NPC92297
0.8505 High Similarity NPC473844
0.8505 High Similarity NPC51947
0.8505 High Similarity NPC473817
0.85 High Similarity NPC151214
0.85 High Similarity NPC191915
0.8476 Intermediate Similarity NPC470167
0.8469 Intermediate Similarity NPC131466
0.8462 Intermediate Similarity NPC80640
0.8462 Intermediate Similarity NPC471254
0.8462 Intermediate Similarity NPC470172
0.8447 Intermediate Similarity NPC41843
0.844 Intermediate Similarity NPC157571
0.8431 Intermediate Similarity NPC74466
0.8431 Intermediate Similarity NPC471241
0.8431 Intermediate Similarity NPC470632
0.8431 Intermediate Similarity NPC470591
0.8426 Intermediate Similarity NPC471431
0.8411 Intermediate Similarity NPC88744
0.8411 Intermediate Similarity NPC207693
0.8396 Intermediate Similarity NPC119628
0.8396 Intermediate Similarity NPC158367
0.8396 Intermediate Similarity NPC158051
0.8381 Intermediate Similarity NPC471253
0.8381 Intermediate Similarity NPC473406
0.8365 Intermediate Similarity NPC108227
0.8365 Intermediate Similarity NPC476839
0.8365 Intermediate Similarity NPC476838
0.8365 Intermediate Similarity NPC475574
0.8365 Intermediate Similarity NPC472081
0.8365 Intermediate Similarity NPC476512
0.8364 Intermediate Similarity NPC97002
0.8362 Intermediate Similarity NPC273962
0.8349 Intermediate Similarity NPC240734
0.8349 Intermediate Similarity NPC91838
0.8349 Intermediate Similarity NPC275668
0.8349 Intermediate Similarity NPC204392
0.8349 Intermediate Similarity NPC274833
0.8349 Intermediate Similarity NPC11035
0.8349 Intermediate Similarity NPC1876
0.8333 Intermediate Similarity NPC22709
0.8333 Intermediate Similarity NPC240125
0.8333 Intermediate Similarity NPC475765
0.8333 Intermediate Similarity NPC412
0.8333 Intermediate Similarity NPC87393
0.8333 Intermediate Similarity NPC258789
0.8333 Intermediate Similarity NPC194310
0.8333 Intermediate Similarity NPC258815
0.8333 Intermediate Similarity NPC241310
0.8333 Intermediate Similarity NPC131841
0.8333 Intermediate Similarity NPC169727
0.8333 Intermediate Similarity NPC475785
0.8333 Intermediate Similarity NPC47567
0.8333 Intermediate Similarity NPC252056
0.8333 Intermediate Similarity NPC91583
0.8318 Intermediate Similarity NPC475630
0.8318 Intermediate Similarity NPC40716
0.8318 Intermediate Similarity NPC138219
0.8318 Intermediate Similarity NPC475234
0.8302 Intermediate Similarity NPC267637
0.83 Intermediate Similarity NPC307167
0.83 Intermediate Similarity NPC210759
0.83 Intermediate Similarity NPC229801
0.8286 Intermediate Similarity NPC114700
0.8286 Intermediate Similarity NPC470029
0.8286 Intermediate Similarity NPC134967
0.8286 Intermediate Similarity NPC310138
0.8273 Intermediate Similarity NPC472719
0.8273 Intermediate Similarity NPC470543
0.8273 Intermediate Similarity NPC207845
0.8269 Intermediate Similarity NPC80417
0.8265 Intermediate Similarity NPC43912
0.8265 Intermediate Similarity NPC140446
0.8257 Intermediate Similarity NPC66513
0.8252 Intermediate Similarity NPC210157
0.8241 Intermediate Similarity NPC262567
0.8241 Intermediate Similarity NPC473688
0.8241 Intermediate Similarity NPC231566
0.8241 Intermediate Similarity NPC471626
0.8224 Intermediate Similarity NPC273189
0.8224 Intermediate Similarity NPC306776
0.8224 Intermediate Similarity NPC184805
0.8224 Intermediate Similarity NPC166079
0.8214 Intermediate Similarity NPC475490
0.8208 Intermediate Similarity NPC139181
0.8208 Intermediate Similarity NPC476837
0.8208 Intermediate Similarity NPC97260
0.82 Intermediate Similarity NPC65550
0.8198 Intermediate Similarity NPC146563
0.8182 Intermediate Similarity NPC272242
0.8182 Intermediate Similarity NPC477073
0.8174 Intermediate Similarity NPC75417
0.8165 Intermediate Similarity NPC8431
0.8158 Intermediate Similarity NPC157868
0.8158 Intermediate Similarity NPC208381
0.8158 Intermediate Similarity NPC469945
0.8158 Intermediate Similarity NPC39211
0.8158 Intermediate Similarity NPC475171
0.8158 Intermediate Similarity NPC114441
0.8158 Intermediate Similarity NPC35405
0.8158 Intermediate Similarity NPC11551
0.8158 Intermediate Similarity NPC6377
0.8158 Intermediate Similarity NPC192791
0.8158 Intermediate Similarity NPC214484
0.8158 Intermediate Similarity NPC473884
0.8158 Intermediate Similarity NPC258592
0.8158 Intermediate Similarity NPC472949
0.8158 Intermediate Similarity NPC309780
0.8158 Intermediate Similarity NPC180550
0.8158 Intermediate Similarity NPC178548
0.8155 Intermediate Similarity NPC476728
0.8148 Intermediate Similarity NPC287269
0.8148 Intermediate Similarity NPC471430
0.8142 Intermediate Similarity NPC477252
0.8137 Intermediate Similarity NPC309866
0.8137 Intermediate Similarity NPC252253
0.8137 Intermediate Similarity NPC45959
0.8137 Intermediate Similarity NPC305418
0.8131 Intermediate Similarity NPC100078
0.8131 Intermediate Similarity NPC327093
0.8131 Intermediate Similarity NPC88469
0.8125 Intermediate Similarity NPC469821
0.8125 Intermediate Similarity NPC54395
0.812 Intermediate Similarity NPC469841
0.812 Intermediate Similarity NPC130229
0.812 Intermediate Similarity NPC469842
0.8119 Intermediate Similarity NPC475878
0.8119 Intermediate Similarity NPC473830
0.8119 Intermediate Similarity NPC204881
0.8113 Intermediate Similarity NPC244969
0.8113 Intermediate Similarity NPC213528
0.8113 Intermediate Similarity NPC94919
0.8103 Intermediate Similarity NPC107966
0.8103 Intermediate Similarity NPC235438
0.8103 Intermediate Similarity NPC40775
0.8103 Intermediate Similarity NPC249848
0.81 Intermediate Similarity NPC82955
0.8073 Intermediate Similarity NPC316930
0.8073 Intermediate Similarity NPC230888
0.807 Intermediate Similarity NPC286347
0.8061 Intermediate Similarity NPC290612
0.8058 Intermediate Similarity NPC62407
0.8058 Intermediate Similarity NPC92196
0.8058 Intermediate Similarity NPC477494
0.8058 Intermediate Similarity NPC287354
0.8058 Intermediate Similarity NPC305808
0.8053 Intermediate Similarity NPC472718
0.8053 Intermediate Similarity NPC137414
0.8053 Intermediate Similarity NPC469823
0.8053 Intermediate Similarity NPC469820
0.8039 Intermediate Similarity NPC149400
0.8039 Intermediate Similarity NPC137004
0.8039 Intermediate Similarity NPC144790
0.8039 Intermediate Similarity NPC172838
0.8039 Intermediate Similarity NPC88962
0.8039 Intermediate Similarity NPC473726
0.8036 Intermediate Similarity NPC477074
0.8036 Intermediate Similarity NPC102619
0.8034 Intermediate Similarity NPC235405
0.8034 Intermediate Similarity NPC30735

  Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC203974 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.8654 High Similarity NPD8170 Clinical (unspecified phase)
0.8304 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.8036 Intermediate Similarity NPD8133 Approved
0.7881 Intermediate Similarity NPD8328 Phase 3
0.7864 Intermediate Similarity NPD8171 Discontinued
0.7679 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.748 Intermediate Similarity NPD7736 Approved
0.7459 Intermediate Similarity NPD7507 Approved
0.7347 Intermediate Similarity NPD6114 Approved
0.7347 Intermediate Similarity NPD6115 Approved
0.7347 Intermediate Similarity NPD6697 Approved
0.7347 Intermediate Similarity NPD6118 Approved
0.7288 Intermediate Similarity NPD6940 Discontinued
0.728 Intermediate Similarity NPD7319 Approved
0.7258 Intermediate Similarity NPD8293 Discontinued
0.7245 Intermediate Similarity NPD6116 Phase 1
0.719 Intermediate Similarity NPD8377 Approved
0.719 Intermediate Similarity NPD8294 Approved
0.7157 Intermediate Similarity NPD3670 Clinical (unspecified phase)
0.7157 Intermediate Similarity NPD3669 Approved
0.7143 Intermediate Similarity NPD6117 Approved
0.7131 Intermediate Similarity NPD8379 Approved
0.7131 Intermediate Similarity NPD8378 Approved
0.7131 Intermediate Similarity NPD8033 Approved
0.7131 Intermediate Similarity NPD8296 Approved
0.7131 Intermediate Similarity NPD8380 Approved
0.7131 Intermediate Similarity NPD8335 Approved
0.713 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7129 Intermediate Similarity NPD1780 Approved
0.7129 Intermediate Similarity NPD1779 Approved
0.7073 Intermediate Similarity NPD6370 Approved
0.7054 Intermediate Similarity NPD1700 Approved
0.7034 Intermediate Similarity NPD8297 Approved
0.7034 Intermediate Similarity NPD6882 Approved
0.7018 Intermediate Similarity NPD4056 Clinical (unspecified phase)
0.7018 Intermediate Similarity NPD4057 Clinical (unspecified phase)
0.696 Remote Similarity NPD7492 Approved
0.6944 Remote Similarity NPD8034 Phase 2
0.6944 Remote Similarity NPD8035 Phase 2
0.6942 Remote Similarity NPD6009 Approved
0.6939 Remote Similarity NPD6113 Clinical (unspecified phase)
0.6923 Remote Similarity NPD6372 Approved
0.6923 Remote Similarity NPD6373 Approved
0.6911 Remote Similarity NPD6319 Approved
0.6911 Remote Similarity NPD6054 Approved
0.6911 Remote Similarity NPD6059 Approved
0.6905 Remote Similarity NPD6616 Approved
0.6897 Remote Similarity NPD6412 Phase 2
0.6885 Remote Similarity NPD7327 Approved
0.6885 Remote Similarity NPD7328 Approved
0.6869 Remote Similarity NPD3703 Phase 2
0.6863 Remote Similarity NPD6928 Phase 2
0.685 Remote Similarity NPD7078 Approved
0.6829 Remote Similarity NPD7516 Approved
0.681 Remote Similarity NPD7128 Approved
0.681 Remote Similarity NPD6402 Approved
0.681 Remote Similarity NPD6675 Approved
0.681 Remote Similarity NPD5739 Approved
0.6807 Remote Similarity NPD6649 Approved
0.6807 Remote Similarity NPD6650 Approved
0.672 Remote Similarity NPD6015 Approved
0.672 Remote Similarity NPD8516 Approved
0.672 Remote Similarity NPD8517 Approved
0.672 Remote Similarity NPD8513 Phase 3
0.672 Remote Similarity NPD8515 Approved
0.672 Remote Similarity NPD6016 Approved
0.67 Remote Similarity NPD3702 Approved
0.6695 Remote Similarity NPD7320 Approved
0.6695 Remote Similarity NPD6881 Approved
0.6695 Remote Similarity NPD6899 Approved
0.6695 Remote Similarity NPD6686 Approved
0.6694 Remote Similarity NPD4632 Approved
0.6667 Remote Similarity NPD5988 Approved
0.6667 Remote Similarity NPD8130 Phase 1
0.661 Remote Similarity NPD5701 Approved
0.661 Remote Similarity NPD5697 Approved
0.6602 Remote Similarity NPD7329 Approved
0.6587 Remote Similarity NPD6921 Approved
0.6587 Remote Similarity NPD7503 Approved
0.6583 Remote Similarity NPD7290 Approved
0.6583 Remote Similarity NPD6883 Approved
0.6583 Remote Similarity NPD7102 Approved
0.6566 Remote Similarity NPD4809 Clinical (unspecified phase)
0.6566 Remote Similarity NPD4808 Clinical (unspecified phase)
0.6552 Remote Similarity NPD8086 Approved
0.6552 Remote Similarity NPD8138 Approved
0.6552 Remote Similarity NPD8082 Approved
0.6552 Remote Similarity NPD8083 Approved
0.6552 Remote Similarity NPD8139 Approved
0.6552 Remote Similarity NPD8084 Approved
0.6552 Remote Similarity NPD8085 Approved
0.6542 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6531 Remote Similarity NPD4267 Clinical (unspecified phase)
0.6529 Remote Similarity NPD6869 Approved
0.6529 Remote Similarity NPD6617 Approved
0.6529 Remote Similarity NPD6847 Approved
0.65 Remote Similarity NPD6012 Approved
0.65 Remote Similarity NPD6013 Approved
0.65 Remote Similarity NPD6014 Approved
0.6496 Remote Similarity NPD8276 Approved
0.6496 Remote Similarity NPD8275 Approved
0.6484 Remote Similarity NPD7604 Phase 2
0.6465 Remote Similarity NPD4789 Approved
0.6457 Remote Similarity NPD5983 Phase 2
0.6441 Remote Similarity NPD8081 Approved
0.6436 Remote Similarity NPD1810 Approved
0.6436 Remote Similarity NPD1811 Approved
0.6417 Remote Similarity NPD6011 Approved
0.6412 Remote Similarity NPD6033 Approved
0.6393 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6393 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6387 Remote Similarity NPD8393 Approved
0.6385 Remote Similarity NPD6336 Discontinued
0.6364 Remote Similarity NPD3699 Clinical (unspecified phase)
0.6364 Remote Similarity NPD3700 Clinical (unspecified phase)
0.6263 Remote Similarity NPD5361 Clinical (unspecified phase)
0.6263 Remote Similarity NPD5360 Phase 3
0.6239 Remote Similarity NPD8418 Phase 2
0.6238 Remote Similarity NPD6081 Approved
0.6238 Remote Similarity NPD5777 Approved
0.623 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6207 Remote Similarity NPD6083 Phase 2
0.6207 Remote Similarity NPD7902 Approved
0.6207 Remote Similarity NPD6084 Phase 2
0.6207 Remote Similarity NPD4755 Approved
0.6198 Remote Similarity NPD8140 Approved
0.6198 Remote Similarity NPD8307 Discontinued
0.619 Remote Similarity NPD6274 Approved
0.6179 Remote Similarity NPD4634 Approved
0.6179 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6174 Remote Similarity NPD7991 Discontinued
0.6172 Remote Similarity NPD7100 Approved
0.6172 Remote Similarity NPD7101 Approved
0.6154 Remote Similarity NPD7638 Approved
0.6142 Remote Similarity NPD7115 Discovery
0.614 Remote Similarity NPD6399 Phase 3
0.6139 Remote Similarity NPD2687 Approved
0.6139 Remote Similarity NPD2254 Approved
0.6139 Remote Similarity NPD7532 Clinical (unspecified phase)
0.6139 Remote Similarity NPD2686 Approved
0.6139 Remote Similarity NPD4244 Approved
0.6139 Remote Similarity NPD4245 Approved
0.6134 Remote Similarity NPD8300 Approved
0.6134 Remote Similarity NPD8301 Approved
0.6116 Remote Similarity NPD6008 Approved
0.6102 Remote Similarity NPD5286 Approved
0.6102 Remote Similarity NPD4700 Approved
0.6102 Remote Similarity NPD7640 Approved
0.6102 Remote Similarity NPD5285 Approved
0.6102 Remote Similarity NPD7639 Approved
0.6102 Remote Similarity NPD4696 Approved
0.6098 Remote Similarity NPD8306 Approved
0.6098 Remote Similarity NPD8305 Approved
0.6094 Remote Similarity NPD6335 Approved
0.6087 Remote Similarity NPD7748 Approved
0.6077 Remote Similarity NPD6908 Approved
0.6077 Remote Similarity NPD8274 Clinical (unspecified phase)
0.6077 Remote Similarity NPD6909 Approved
0.6061 Remote Similarity NPD4224 Phase 2
0.6048 Remote Similarity NPD8087 Discontinued
0.604 Remote Similarity NPD3698 Phase 2
0.6031 Remote Similarity NPD8080 Discontinued
0.6019 Remote Similarity NPD3181 Approved
0.6017 Remote Similarity NPD5696 Approved
0.6016 Remote Similarity NPD8174 Phase 2
0.6016 Remote Similarity NPD6317 Approved
0.6 Remote Similarity NPD5226 Approved
0.6 Remote Similarity NPD896 Approved
0.6 Remote Similarity NPD898 Approved
0.6 Remote Similarity NPD4633 Approved
0.6 Remote Similarity NPD5211 Phase 2
0.6 Remote Similarity NPD5225 Approved
0.6 Remote Similarity NPD897 Approved
0.6 Remote Similarity NPD7632 Discontinued
0.6 Remote Similarity NPD5224 Approved
0.5985 Remote Similarity NPD6067 Discontinued
0.5984 Remote Similarity NPD4767 Approved
0.5984 Remote Similarity NPD4768 Approved
0.5983 Remote Similarity NPD4697 Phase 3
0.597 Remote Similarity NPD8074 Phase 3
0.5969 Remote Similarity NPD6313 Approved
0.5969 Remote Similarity NPD6314 Approved
0.596 Remote Similarity NPD3171 Clinical (unspecified phase)
0.595 Remote Similarity NPD5174 Approved
0.595 Remote Similarity NPD5175 Approved
0.5948 Remote Similarity NPD7900 Approved
0.5948 Remote Similarity NPD7901 Clinical (unspecified phase)
0.5938 Remote Similarity NPD6868 Approved
0.5935 Remote Similarity NPD5954 Clinical (unspecified phase)
0.5922 Remote Similarity NPD4758 Discontinued
0.5917 Remote Similarity NPD5223 Approved
0.5913 Remote Similarity NPD7515 Phase 2
0.5902 Remote Similarity NPD5141 Approved
0.5897 Remote Similarity NPD5695 Phase 3
0.5891 Remote Similarity NPD8137 Clinical (unspecified phase)
0.5888 Remote Similarity NPD4802 Phase 2
0.5888 Remote Similarity NPD4238 Approved
0.5888 Remote Similarity NPD5364 Discontinued
0.5888 Remote Similarity NPD3671 Phase 1
0.5887 Remote Similarity NPD4730 Approved

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data